What To Do in Pittsburgh in May 2025

Live life in full bloom this month with tasty food celebrations, creative local markets, an indie bookstore crawl, curious new exhibits, and more 🌼

🚲 Gear Up for Bike to Work Day

On May 15, BikePGH is hosting Commuter Cafés at three posts throughout the city so you can snag free treats on your way to or from work. Find locations in Oakland, Downtown, and the Strip District with goodies from Convive Coffee, Brooklyn Bagel, East End Food Co-op, De Fer Coffee & Tea, and Kaya.

🏡 Be Nebby on a House Tour

Ever wonder what that gorgeous historic house looks like on the inside? Take a self-guided walking tour of 10 unique homes in Highland Park — from grand Victorians to stately Colonials. Proceeds go to the Highland Park Community Council.

🪴 Shop at Pop-Up Markets & Plant Sales

Gift your mom or a mother figure something from Phipps' annual plant and garden sale May 9-10. Or celebrate Mother's Day at the Lawrenceville Market House May 10 with wine, a flower bar, $2 donuts, and tattoos! Looking for more floral fun? Mosey through the Sweetwater Blooms market May 17.

👀 Tip: Search for more treasures at Union Project's Mother of All Pottery Sales, the return of Neighborhood Flea May 11, or WorkshopPGH’s Garage Sale & Flea May 17.

🪩 Dance the Night Away

In Bed by Ten is celebrating its ten-year anniversary with a bash at Spirit May 23. Move to tunes from the 1970s to the 2000s, spun by four different DJs, and drink a special anniversary beer made in collaboration with Two Frays Brewing. A portion of proceeds go to Prevention Point Pittsburgh.

🎶 More events for movin’ and groovin’: Jellyfish, Title Town Soul and Funk Party, Steel Guitar Jam, Millvale Music Festival, and Celestial Bodies Gemini dance party.

⚽ Cheer On the Riveters

Pittsburgh is officially a women’s soccer town! The Pittsburgh Riveters will play their first game at Highmark Stadium May 16 against the Cleveland Force. The first 500 fans get a commemorative inaugural game centerpiece. See their game schedule for promotional nights.

📚 Find New Reads at Book Events

This month is for fans of literary arts! Find readings, improv performances, poetry slams, local jazz legends, and more at City of Asylum’s Jazz Poetry Month, May 1-22.

Lolev Beer in Lawrenceville is hosting a book fair May 10 featuring local authors, indie bookstores, and banned books.

It’s also the start of the Great Pittsburgh Book Crawl — nine straight days of book shopping, May 10-18. Grab your book crawl passport at any participating store, and get stamps to win raffle prizes.

The book festivities culminate with the Greater Festival of Books at Carnegie Library in Oakland May 31. The celebration highlights local and nationally-recognized authors, dozens of poets, bookstores, and publishers.

🍓 Dig In at Food Fests & Farmer’s Markets

Grab your tote! It’s time to get farm fresh produce, homemade cheese, and delectable jam and honey. Farmers market season kicks off May 4 in Bloomfield; the North Side market starts May 16, and Lawrenceville debuts May 20.

We’re also ushering in food festival season! Get your fill at the Pierogi Festival, Oyster Fest, and more tasty events. Check out this lineup 📌

📣 Reimagine Cultural Spaces

Kelly Strayhorn Theater’s Owning Our Future symposium is all about empowering BIPOC artists. Take in panel discussions, keynote addresses, and performances May 15-18 — like a documentary about gentrification in East Liberty or an event with a local artist who created an app that maps Pittsburgh’s Black history.

👀 Discover ‘Hidden History’

The Heinz History Center’s newest exhibit tells the story of Pittsburgh’s past through rarely and never-before-displayed objects and artifacts. Don’t miss the opportunity to peek at items from iconic institutions like The Original Hot Dog Shop, Primanti Bros., Kaufmann’s, and Kennywood.